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Thursday, January 29, 2015

“2015 Drug Design & Delivery Symposium:

Designing Better Drug Candidates”

Dr. Paul Leeson, Director, Paul Leeson Consulting, Ltd.

Dr. Rick Connell, Vice President, External Research Solutions, Pfizer

Thursday, February 5, 2015

“Natural Product Chemistry: Benefits of

Pterostilbene on Health, Memory, and Anxiety”

Dr. Agnes Rimando, Research Chemist, U.S. Department of Agriculture

Dr. Dave Harwell, Assistant Director of Industry Member Programs, American

Chemical Society

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Pacifichem 2015 www.pacificchem.org

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Learn more about the technical program and subject areas covered visit: www.pacifichem.org

Abstract submission is open from January 1 – April 3, 2015

THE INTERNATIONAL CHEMICAL CONGRESS

OF PACIFIC BASIN SOCIETIES

Honolulu, Hawaii DECEMBER 15 - 20, 2015

12

“3D Printing: From Molecules to Manufacturing”

Submit Your Abstracts to Pacifichem 2015 today! Find out more at www.pacifichem.org

www.acs.org/acswebinars Slides available Now! Recordings will be available to ACS members after one week

Dr. Timothy Long Professor of Chemistry and Director of

Macromolecules and Interfaces Institute,

Virginia Tech

Dr. Chris Williams Associate Professor of Mechanical

Engineering and Asst. Director of


Virginia Tech

Dr. Mark Jones Executive External Strategy

and Communications Fellow,

Dow Chemical

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Christopher B. Williams

Associate Director, Macromolecules & Interface Institute

Department of Mechanical Engineering

Virginia Tech

[email protected]

3D Printing: From Molecules to Manufacturing

Timothy E. Long

Director, Macromolecules & Interface Institute

Department of Chemistry

Virginia Tech

[email protected]

The Virginia Tech Team

Tim Long The Long Group

http://www.tlong.chem.vt.edu/

Chris Williams DREAMS Lab

http://www.me.vt.edu/dreams @DREAMSlab

http://www.tlong.chem.vt.edu/

http://www.me.vt.edu/dreams



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http://www.dezeen.com/2013/05/29/3d-printed-robohand-helps-children-born-without-fingers/

http://fineprintnyc.blogspot.com/2013/05/3d-printed-implant-saves-babys-life.html

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http://thehightechsociety.com/3d-printing-change-face-poverty-stricken-nations/

http://www.the-scientist.com/?articles.view/articleNo/37270/title/Organs-on-Demand/

http://www.newscientist.com/data/images/ns/cms/dn20737/dn20737-1_300.jpg

https://www.solidconcepts.com/content/images/selective-laser-sintering-sls-015.jpg

Challenge, Opportunity & Invitation Additive Manufacturing needs:

Larger catalog of working materials

Structure-Property-Process understanding

Chemistry opportunities:

Tailoring rheology/viscosity for AM platforms with new macromolecular architectures

Understanding intermolecular interactions at interfaces, surfaces, and interfacial phenomena

Physical properties of layered architectures

New orthogonal synthetic methods and photo-reactive monomers/oligomers

http://wohlersassociates.com/roadmap2009.html

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Molecules to Manufacturing

Opportunity to realize breakthrough products via concurrent design of novel polymer chemistry, part geometry, and manufacturing process.

Structural Parameters for Polymeric Materials in Additive Manufacturing

Molecular Weight and Molecular Weight Distribution

Chemical Composition

Chain Isomerism/Stereochemistry

Morphology

Topology

Rheology (solution and melt)

Surface Features

Polymer Additives

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Webinar Outline

Additive Manufacturing Overview

Additive Manufacturing Materials & Processes

Extrusion

Photopolymerization

Vat-based & Jetting

Powder Bed Fusion

Binder Jetting

Summary

http://www.compassdude.com/i/topographic-map.jpg

Additive Manufacturing

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http://www.compassdude.com/i/topographic-map.jpg

http://upload.wikimedia.org/wikipedia/commons/6/68/Fotothek_df_n-20_0000140_Zerspannungsfacharbeiter.jpg

vs.

ASTM F2792-10

Subtractive Additive

When was the first “3D printing” technology commercialized?

1970s

1980s

1990s

2000s

2010s

Instantaneous Audience Question

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AM Technologies: Classification

ASTM F2792:12a


ASTM F2792:12a

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Material Extrusion Processes

media1.wmv

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Entering the Viscous Melt State

Provide heat to induce polymer flow

Need to maintain constant temperature

Avoid overheating:

Polymers degrade at high temperatures and can leave residue

Thermoplastic Polymers for Extrusion

30 Gibson, I.; Rosen, D. W.; Stucker, B.; Springer: New York, 2010, pg. 159

Images - http://en.wikipedia.org/wiki/Fused_deposition_modeling

Polymer Type Chemical Structure Properties

Acrylonitrile-Butadiene-Styrene (ABS)

High toughness and impact resistance

Polysulfones Heat/chemical resistance, dimensional

stability

Polycarbonates High impact resistance/tensile strength,

low scratch resistance

Polyetherimides

High temp applications (Tg = 216 °C),

similar to PEEK

Polyesters Biocompatible and biodegradable

Any thermoplastic material with proper melt viscosity is potentially suitable for extrusion

http://blog.lib.umn.edu/thors394/3701/assets_c/2

013/10/DSC_2569-thumb-800x529-167617.jpg

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Morphology of Thermoplastics: Study of Structure What are the details of the structure of the solid?

Crystalline Semicrystalline Amorphous

Melting @ Tm

Heat of Fusion Stronger Forces Correlated Structure

Glass Transition No Heat of Fusion Free Volume Amorphous Form

Melt Rheology Considerations

Viscosity of Polymers as a

Function of Molecular Weight

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Relationship of Molecular Weight to

Mechanical Properties and Rheology

Properties increase, then essentially plateau with MW at Me, entanglement MW

Melt Viscosity proportional to 3.4 power of weight average MW.

“Property” e.g., Tg

M.W.

0 (Zero shear melt Viscosity)

Me = MW where entanglements become important Tg ~ Tg - Constant / Mn

Me

Advancements in Extrusion

http://cloudwiser.wordpress.com/2014/09/15/local-motors-3d-prints-a-car-live-at-imts-3d-printing-industry/

http://www.envisiontec.de/

http://craft.usc.edu/CC/modem.html

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Which of the following materials often used in 3D Printing are thermoplastics?

Amorphous polymers

Semi-crystalline polymers

Hydrogels

Crosslinked epoxies

Block copolymers


ASTM F2792:12a

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Vat Photopolymerization

Scanning Mirrors

Stereolithography (3D Systems)

http://www.pi-castings.co.uk/_includes/images/global/RPQuickCastmodelsRacingCar.jpg

Mask Projection mStereolithography

Projected UV light selectively cures photopolymer

http://pubs.acs.org/doi/abs/10.1021/mz5006316

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Material Jetting: Stratasys PolyJet

Stratasys PolyJet Material Jetting

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UV-Curable Photopolymers for Stereolithography

41 Gibson, I.; Rosen, D. W.; Stucker, B.; Springer: New York, 2010, pg. 63-67

Functional Group Type

Acrylate / Methacrylate

Epoxy Vinyl Ether

Curing Mechanism

Free Radical Cationic Cationic

Chemical Structure

Examples

Polymer backbone can contain any of: - Linear/cyclic aliphatics - Aromatics - Polyurethanes/ureas - Polyesters - Polyethers - Polycarbonates

Most versatile AM method for polymeric materials

Any liquid polymeric (oligomeric) material is suitable for stereolithography.

A Smart Swap™ accessory offers rheological characterization of UV curable materials

TA Instruments-Discovery Hybrid Accessories http://www.tainstruments.com

UV Curing Accessory

High-pressure mercury light source for UV radiation UV wavelengths in the range of 320 to 500 nm

Smart Swap assembly with light source mount, collimator, and 5 mm light guide

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1.E+1

1.E+2

1.E+3

1.E+4

1.E+5

1.E+6

1.E+7

0 50 100 150 200 250 300 350

G'

or

G''

(P

a)

time (s)

L61 20mW/cm2

L61 5 mW/cm2

UV Light

Photo-rheology accelerates discovery for cure time and viscosity optimization

DHR-2: 20 mm parallel plate, UHP, 500 um gap, 10 Hz, 0.05% strain G’

G’’

SEM reveals architectural definition for Pluronic L-61 scaffolds

1 mm

500 µm 500 µm

500 µm

SEM: NEO Scope JCM 5000

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SL Materials: Acrylates & Epoxies

Acrylate (acrylic monomer + free radical photoinitiator)

Faster polymerization

Warping

Poor material properties

Epoxy (epoxy monomer + cationic photoinitiator)

Slow

Sensitive to impurities (e.g., water)

Viscous

Good material properties

SL Materials: Acrylates & Epoxies

Commercial materials are combinations of acrylates and epoxies.

Acrylates reduces energy required for cationic reaction

Epoxy aides free-radical reaction (acts as a plasticizer)

Acrylate and epoxy monomers do not react with one another. Result is interpenetrating polymer network.

Variety of additives to stabilize resin, adjust viscosity, etc.

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Which of the following parameters does NOT influence the rate of the photochemical curing reaction in a stereo lithographic process?

Glass transition temperature of the final polymer

Photo-initiator concentration

Acrylate concentration

Phase of the moon


Phosphonium monomers displayed ionic liquid behavior with bulky counterions

48

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Mask projection micro-stereolithography successfully 3D prints phosphonium ILs

3D Printer: UV LED 365 nm, build surface intensity 5 mW/cm2, Digital micro image device 1080 p

O

O

O

O

x

y

P T f 2 N

z

Poly(PEGDMA90-co -TOPTf2N10) with 0.25 wt% Tinuvin® increases print resolution, printability, and structural definition


100 mm 500 mm 1 mm

0.5 mm 0.1 mm

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Polyester cylinders provide structural advantages in tissue-engineered scaffolds


Outer layer: Elastic and collagen fibers

Inner layer: Endothelium Middle layer: Smooth muscle & elastic tissue

lumen

Suspension Photo-polymerization

ba

Images of jetted QD Nanoink in (a) visible and (b) UV light

Elliott et al., 2013, Advanced Engineering Materials, 15(10), 903-907.

Emerging research in photo-polymerization of particulate suspensions

Example:

Material Jetting of Quantum Dot acrylate suspension

“Programmable Matter” for anti-counterfeiting applications

Stochastic arrangement of nanoparticles in droplet create unique identifier that cannot be replicated

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ASTM F2792:12a

Powder Bed Fusion

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“Powder Bed Fusion Additive Manufacturing;" J. P. Kruth, KU Leuven University, Belgium

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ASTM F2792:12a

Binder Jetting

www.exone.com

• Binder is selectively jetted into powder bed

• Powder for next layer is swept onto bed via a roller

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Binder Jetting

Starch / Plaster Foundry Sand

Ceramics (e.g., B4C)

Metals (e.g., steel; Cu)

Binder Jetting Materials

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Key Takeaway

Additive Manufacturing

+ Novel Polymer Synthesis

+ Tailored Part Geometry

= Can displace what is possible with conventional materials and traditional manufacturing processes

Acknowledgements: Sponsors

National Science Foundation

Air Force Research Laboratory

Virginia Center for Innovative Technology

VT Institute for Critical Technology & Applied Science

Army Research Office, ILEAD MURI

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Acknowledgements: Collaborators

Students:

Nick Meisel (PhD Candidate)

Nicholas Chartrain (PhD Student)

Amelia Elliott (PhD 2014)

Nancy Zhang (PhD 2012)

Ashley Nelson (PhD Candidate)

Faculty:

Thomas Campbell (VT, ICTAS)

Vicki Long (VT, Chemistry)

Olga Ivanova (Postdoc 2014)

Blake Perez (MS 2014)

Phillip Lambert (MS 2014)

Alison Schultz (PhD Candidate)

Justin Sirrine (PhD Candidate)

64






Virginia Tech




Virginia Tech



Dow Chemical

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Chemical Society

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Virginia Tech




Virginia Tech



Dow Chemical

Be a featured fan on an upcoming webinar! Write to us @ [email protected]

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How has ACS Webinars benefited you?

®

“ACS Webinars benefits me because the topics are

timely, I can attend during workday, and the

information can be put to immediate use. Our

Institute is limiting travel to meetings so webinars

ARE the way I continue my career development.”

Trudy Holyst, M.S.

Senior Lab Technologist,

Protein Chemistry Core Lab,

Blood Research Institute

1/22/2015

35

69


@acswebinars

youtube.com/acswebinars

Benefits of ACS Membership

70 www.acs.org/2joinACS

Chemical & Engineering News (C&EN) The preeminent weekly news source.

NEW! Free Access to ACS Presentations on Demand® ACS Member only access to over 1,000 presentation recordings from recent ACS meetings and select events.

NEW! ACS Career Navigator Your source for leadership development, professional education, career services, and much more.

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